Pyridine-1,3,4-Thiadiazole-Schiff Base Derivatives, as Antioxidant and Antimitotic Agent: Synthesis and in Silico ADME Studies

Abstract

An efficient method developed for the synthesis of asymmetric (S)-N-benzylidene-2-(benzyloxy)-1-(5-(pyridin-2-yl)-1,3,4-thiadiazol-2-yl)ethanamine derivatives with excellent yield in short reaction time. The antioxidant and antimitotic activities were estimated and strongly correlated with the potential of Ascorbic acid and Methotrexate respectively. All the synthesized molecules were characterized using various spectral techniques including FTIR, ¹H NMR, ¹³C NMR, and Mass spectrometry. The drug-likeness properties were studied using in silico ADME parameters. All the compounds have an acceptable range of values which indicated good drug-like characteristics based on Lipinski's rule of five and to be orally active. The present method is quite easy along with simple operation and offers many benefits including short reaction time, easy work-up, excellent yield, reduced waste production as well as cost effective. In addition structure-activity relationships of AP-1 to AP-10 derivatives have been described.

Graphical Abstract

Keywords:

• Antioxidant
• antimitotic
• asymmetric synthesis
• in silico ADME parameters
• structure-activity relationships

Acknowledgments

The authors are gratefully acknowledged to Dr. Rahul Ingle, Institute of Drug Metabolism and Pharmaceutical Analysis, Zhejiang University, Hangzhou (China) and Dr. Gajanan Sonawane, Principal, Rajesh Bhaiyya Tope College of Pharmacy, Aurangabad (India) for his kind support during work. The Authors also gratefully acknowledged to Ms. Rajashri Pund-Nale, Department of Zoology, Bhaskar Pandurang Hivale Education Society’s Ahmednagar College, Ahmednagar for support during biological evaluation.

Disclosure statement

The authors declare no conflict of interest.

Correction Statement

This article has been republished with minor changes. These changes do not impact the academic content of the article.